N,N-Dimethylglycine → HCID 118272045, compound

HRID 588163Notes

Reaction equation

HRID 588163 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8](I)=[N:9][N:10]([C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:4]=2[CH:3]=1.[C:31]1([OH:37])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)CC(O)=O>O1CCOCC1.[Cu]I>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8]([O:37][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[N:9][N:10]([C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 673N,N-DimethylglycineHCID 996PhenolHCID 10796Cesium carbonateHCID 895258586-Chloro-3-iodo-1-trityl-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 118272045HCID 118272045, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

6-chloro-3-iodo-1-trityl-1H-pyrazolo[4,3-c]pyridine (160 mg, 0.307 mmol), phenol (43.3 mg, 0.460 mmol), copper(i) iodide (5.84 mg, 0.031 mmol), cesium carbonate (200 mg, 0.613 mmol) and N,N-dimethylglycine (9.49 mg, 0.092 mmol) were taken up in 1,4-Dioxane (2.0 ml) in a 25 mL microwave vial. The vial was evacuated and back-filled with N2 (3×) and the reaction mixture was allowed to stir at 100° C. for 6 h. NH4OH was added into the reaction mixture and extracted with EtOAc (2×). The combined organic extracts were washed with water, brine and dried over Na2SO4. After concentration the crude product was purified on silical gel 0-50% EtOAc/Hexanes and yielded 6-chloro-3-phenoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine (120 mg, 0.246 mmol, 80% yield). MS: [M+H]+ m/z 488.

Workup

  1. customThe vial was evacuated
  2. additionback-filled with N2 (3×)
  3. additionNH4OH was added into the reaction mixture
  4. extractionextracted with EtOAc (2×)
  5. washThe combined organic extracts were washed with water, brine
  6. dry with materialdried over Na2SO4
  7. concentrationAfter concentration the crude product
  8. customwas purified on silical gel 0-50% EtOAc/Hexanes

Sources & evidence

ORD record
ord-ff1c937d3718488bb34eed3ec162ef3e
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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